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Assessment of flavonoids and volatile


compounds in tea infusions of water lily flowers
and their antioxidant activities

ARTICLE in FOOD CHEMISTRY NOVEMBER 2015


Impact Factor: 3.26 DOI: 10.1016/j.foodchem.2015.04.032

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Retrieved on: 04 August 2015
Food Chemistry 187 (2015) 2028

Contents lists available at ScienceDirect

Food Chemistry
journal homepage: www.elsevier.com/locate/foodchem

Assessment of avonoids and volatile compounds in tea infusions


of water lily owers and their antioxidant activities
Dan-Dan Yin a,b,1, Ru-Yu Yuan a,c,1, Qian Wu a,c, Shan-Shan Li a,b, Shuai Shao a,c, Yan-Jun Xu d,
Xiang-Hong Hao d, Liang-Sheng Wang a,
a
Key Laboratory of Plant Resources and Beijing Botanical Garden, Institute of Botany, Chinese Academy of Sciences, Beijing 100093, China
b
University of Chinese Academy of Sciences, Beijing 100049, China
c
College of Horticulture, Nanjing Agriculture University, Nanjing 210095, China
d
Department of Applied Chemistry, China Agricultural University, Beijing 100094, China

a r t i c l e i n f o a b s t r a c t

Article history: Water lily, a member of the Nymphaeaceae family, can be made into tea on the basis of outstanding fra-
Received 30 November 2014 grance characteristics and health care functions. In this study, 16 avonoids were identied and quanti-
Received in revised form 10 April 2015 ed in tea infusions prepared from the petals of 33 water lily cultivars using HPLCDAD and HPLCESI-
Accepted 12 April 2015
MS/MS. The infusions were analyzed with HS-SPME coupled with GCMS; 29 volatile compounds were
Available online 18 April 2015
detected, of which nine were found to be scent components. The cultivars were clustered into three clus-
ters characterized according to scent components. The Conqueror and Virginia cultivars had the highest
Keywords:
antioxidant activities. The concentrations of polyphenols and avonoids showed signicant positive
Water lily
Tea infusion
correlations with antioxidant activity as measured by DPPH, ABTS+, and FRAP assays. This study is valu-
Flavonoids able for a fuller understanding of this important tea and can also be used for the development of water
Volatile compounds lily.
Antioxidant activity 2015 Published by Elsevier Ltd.

1. Introduction as tea. It therefore has both full-bodied fragrance and a deep tea
infusion color. Water lily has great developing potential in the
Water lily (a herb of the genus Nymphaea, family functional process of tea beverage industry with both high
Nymphaeaceae), a perennial aquatic ower plant, is divided into ornamental value and health care functions.
two ecological groups based on geographic occurrence, namely Flavonoids, which occur widely in plants, are an important class
the tropical water lily group and the hardy water lily group of plant natural products. Many avonoids have exhibited obvious
(Huang, Deng, Li, & Li, 2009). Water lily is widely used as an physiological activities in the human body, such as anti-ulcer,
ornamental plant in landscaping and is also used in water purica- antibacterial, anti-inammatory, anti-hyperlipidemia, and analge-
tion applications. Water lily owers, roots and stems are also used sia activities (Zafra-Stone et al., 2007). Research by Zhao et al.
in the medical domain, and have been shown to have anesthetic, (2014) showed that water lily contains polyphenols such as
roborant, astringent, and diuretic properties, and are used as a kaempferol, quercetin, and gallic acid, compounds known to
therapy for nephritis (Agnihotri et al., 2008; Daboor & Haroon, extend the shelf life of food, inhibit lipid oxidation, restrain bacter-
2012). Totally, 74 avonoids and phenolic acid compounds have ial growth, resist aging, and prevent tumor growth and cardio-
been isolated from genus Nymphaea in previous works (Zhao, Xu, vascular disease. Additionally, water lily contains quercetin and
Ji, Gu, & Li, 2014). Due to the polyphenols that it contains, water chalcone compounds that have been reported to possess antioxi-
lily is regarded as a natural source of antioxidant (Kerio, dant and antitumor activity (Nasi, Hashemi, & Rajabi, 2008;
Wachira, Wanyoko, & Rotich, 2013). Scented tea, a unique category Yagura et al., 2008). According to Agnihotri et al. (2008), the
of Chinese tea, is made from elegant and aromatic owers as well EtOAc fraction of Nymphaea caerulea owers can be used as a
new natural product for the treatment of oxidative stress-related
diseases. Previous studies in this vein have focused primarily on
Corresponding author at: No. 20 Nanxincun, Xiangshan, Beijing 100093, China. water lily itself, paying little attention to teas prepared from water
Tel.: +86 10 6283 6654; fax: +86 10 6259 0348.
lilies (Yuan et al., 2014; Zhu, Wang et al., 2012; Zhu, Zheng et al.,
E-mail address: wanglsh@ibcas.ac.cn (L.-S. Wang).
1 2012). Therefore, it is of great signicance to identify the avo-
These authors contributed equally to this work and are considered as joint rst
authors. noids and evaluate the antioxidant activity in tea infusions of

http://dx.doi.org/10.1016/j.foodchem.2015.04.032
0308-8146/ 2015 Published by Elsevier Ltd.
D.-D. Yin et al. / Food Chemistry 187 (2015) 2028 21

water lily in order to lay a scientic foundation for the develop-


ment and utilization of water lily tea.
Tea fragrance is one of the most important factors impacting the
characteristics and quality of tea, contributing from 25% to 40% of
organoleptic quality (Wang, 2006). Since water lily contains abun-
dant volatile compounds with desirable fragrances, its con-
tributions to tea infusions merit study (Yuan et al., 2014).
Volatile compounds in tea contribute to its fragrance and include
alcohols, hydrocarbons, aldehydes, ketones, esters, nitrogenous
compounds, and phenolic compounds (Du et al., 2014). It is impor-
tant to characterize how the scented components differ from vola-
tile compounds in water lily tea. Solid-phase microextraction
(SPME) in headspace mode (HS) has an excellent performance
record for the extraction and analysis of volatile compounds. It is
an ideal sample preparation technique because it is fast, solvent-
free, and cost-effective (Yang, Baldermann, & Watanabe, 2013).
In this study, we identied and quantied a number of avo-
noids from tea infusions of 33 water lily cultivars using high-per-
formance liquid chromatography (HPLC) with photodiode array
detection (DAD) and electrospray ionization mass spectrometry
(ESI-MS). Assays of 1,1-diphenyl-2-picrylhydrazyl radical (DPPH),
2,20 -azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) diammo-
nium salt (ABTS+), and ferric reducing antioxidant potential
(FRAP) are widely used to detect the antioxidant activity of extracts
or single material (Benzie-Iris & Strain, 1996; Ozgen, Reese, Tulio,
Scheerens, & Miller, 2006). SPMEGCMS was used to analyze
volatile compounds in the water lily tea infusions. Furthermore,
the 33 cultivars were classied into three groups using cluster
analysis based on specic scent components and associated fra-
grances. Additionally, we employed three assay types to evaluate
the relationships of total polyphenol content (TPC) and volatile
compounds with antioxidant activities. We anticipate that this
study will help characterize the edible and medicinal value of
water lily and provide a theoretical foundation for the develop-
ment of water lily scented tea in the future.

2. Materials and methods

2.1. Plant materials Fig. 1. HPLC chromatograms at 350 nm of water lily tea infusions. The upper gure
is the chromatogram of the Lausanne cultivar (A). The lower gure is LanHe (B).
Peak identication information is detailed in Table 1.
Thirty-three water lily cultivars were used in this study and
they were divided into two ecological groups. The tropical water
lily group included 21 cultivars: Steven Strawn (1), Ray Davies 12 h. 0.5 g of dry petals, chosen at random from each entire ower,
(2), Lausanne (3), Arethusa (4), Perrys Baby Red (5), Aame was steeped for 10 min in 100 ml of hot water. These and subse-
(6), Alba (7), Princosi (8), Somptuosa (9), Venusta (10), quent procedures were repeated three times for each cultivar.
Conqueror (11), Hollandia (12), Madame Wilfron Gonnere
(13), Sultan (14), Rembrandt (15), Marliacea Carnea (16),
2.2. Collection of volatiles
Newton (17), Celebration (18), Rene Gerard (19), Ellisina (20),
and Virginia (21). The hardy water lily group included 12 culti-
Ten milliliters of the tea infusion soup was aliquoted into a
vars: 9 (22), Roxburgh (23), Ai Ji Bai (24), Lan He (25), 18
brown glass vial (40 mL) and enclosed with a plastic cap with a
(26), America (27), Hu Die Lan (28), Subra (29), Royal Purple
polytetrauoroethylene septum. Volatile compounds were
(30), Mexicana Zuccarni (31), Zanzibar (32), and Fo Shou Lian
extracted by headspace SPME using a 100 lm polydimethyl-silox-
(33). Numbers in parentheses indicated the number of water lily
ane coated ber attached to a manual SPME holder (Supelco,
cultivars in Fig. 2, Tables 2 and 3. The plants were grown in the
Bellefonte, PA, USA). The ber was exposed to each sample by
lotus germplasm nursery of the Beijing Botanical Garden at the
manually penetrating the septum for 30 min at room temperature
Institute of Botany of the Chinese Academy of Science (IBCAS) in
(20 C). The ber was then introduced into the injection port of the
Beijing, China. These cultivars originated from locations all over
GC, which was set at 250 C. The bers were conditioned in the GC
the China. Each cultivar was planted in the same size cylinder
injection port for 30 min at 250 C before volatile collection. The
(diameter 40 cm; height 30 cm) and placed in the same sized pool
carrier gas ow rate was 0.9 mL min1 without diversion.
(140 cm  140 cm  70 cm). The cultivation conditions included
fertilization, irrigation, and pest control measures, and these were
the same for each cultivar. Three fully expanded ower petals (the 2.3. SPMEGCMS
rst day after owering) as three repeats were collected from each
cultivar in the morning between ve and seven oclock and imme- The analysis was carried out using a gas chromatograph-mass
diately processed; sampling took place in May of 2013. In order to spectrometer (GC6890N/MS5973, Agilent) tted with a HP-5MS
facilitate the comparison analyses, petals were freeze-dried for capillary column (5% phenyl methyl siloxane, 30 m  0.25 mm
22 D.-D. Yin et al. / Food Chemistry 187 (2015) 2028

Fig. 2. TPC and antioxidant activity (DPPH, ABTS+ and FRAP) of each sample (mg g1 DW) (mean SE, n = 3) with the reference standards BHT, GA, Vc, and Trolox.

Table 1
HPLCDAD and HPLCESI-MS analysis of avonoids in the tea infusions of water lily owers as well as the characterization and tentative identication.

No. Identication/tentative identication tR (min)a kmax (nm)b ESI-PI MS/MS2 (m/z) ESI-NI MS/MS2 (m/z)
+ +
f1 Chrysoeriol 7-O-glucoside 6.905 267, 344 485[M+Na] , 301[Y0] 463[MH], 299[Y0]
f2 Isorhamnetin 3-O-glucoside 8.260 253, 268, 353 501[M+Na]+, 479[M+H]+, 317[Y+0] 477[MH], 315[Y
0]
f3 Isorhamnetin 3-O-galactoside 8.823 253, 266, 348 501[M+Na]+, 479[M+H]+, 317[Y+0] 477[MH], 315[Y
0]
f4 Quercetin 3-O-rhamnoside 18.175 257, 349 471[M+Na]+, 303[Y+0] 447[MH], 
301[Y0 ], 300[Y0H]
f5 Chalcononaringenin 2-O-galactoside 18.735 250, 366 457[M+Na]+, 273[Y+0] 433[MH], 271[Y
0]
f6 Naringenin 7-O-galactoside 19.473 284, 330 457[M+Na]+, 273[Y+0] 433[MH], 271[Y
0]
f7 Quercetin 7-O-galactoside 21.042 251, 329, 366 487[M+Na]+, 465[M+H]+, 303[Y+0] 463[MH], 301[Y
0]
f8 Isorhamnetin 3-O-rhamnoside 22.622 257, 263, 347 485[M+Na]+, 317[Y0+] 447[MH], 315[Y0]
f9 Kaempferol 3-O-glucosyl-(1 ? 2)-rhamnoside 22.660 266, 348 617[M+Na]+, 449[M+H146]+, 287[Y+0] 593[MH], 447[M+H146], 285[Y 0]
f10 Quercetin 7-O-galactoside 23.590 272, 354 487[M+Na]+, 303[Y+0] 463[MH], 301[Y
0]
f11 Chrysoeriol 7-O-galactoside 29.318 267, 344 485[M+Na]+, 463[M+H]+, 301[Y+0] 461[MH], 
299[Y0 ]
f12 Isorhamnetin 7-O-galactoside 30.420 268, 350 479[M+H]+, 317[Y+0], 163[B1+] 477[MH], 315[Y
0]
f13 Isorhamnetin 7-O-xyloside 33.375 252, 268, 352 471[M+Na]+, 317[Y+0] 477[MH], 315[Y
0]
f14 Isorhamnetin 3-O-xyloside 36.130 252, 268, 352 471[M+Na]+, 449[M+H]+, 317[Y+0] 447[MH], 285[Y0]
00
f15 Kaempferol 3-O-(2 -acetylrhamnoside) 38.343 265, 343 497[M+Na]+, 287[Y+0] 473[MH], 285[Y
0 ], 284[Y0H]
.

f16 Kaempferol 7-O-galactosyl-(1 ? 2)-rhamnoside 39.233 266, 348 617[M+Na]+, 449[M+H146]+, 287[Y+0] 593[MH], 285[Y
0]

a
tR, retention time.
b
kmax, the maximum absorption wavelength.

i.d., 0.25 lm lm thickness, Agilent). Volatile compounds on the ionization potential of mass selective detector was 70 eV and the
ber were desorbed by exposing the ber in the GC injector port scanning range was 30540 amu. The compound identication
for 3 min with a splitless injection. Helium was used as the carrier was based on comparison of analyte mass spectra with the
gas at a ow rate of 1.0 mL min1. The initial oven temperature NIST98 database using G1701BA ChemStation software (Agilent,
was maintained at 40 C for 2 min and then raised to 110 C at USA). Ten microliter of 0.33 mg mL1 3-octanol was used as an
the rate of 4 C min1. Following a hold at 110 C for 2 min, the internal standard compound for quantitative analysis. The calcula-
temperature was increased to 150 C at the rate of 3 C min1 tion formula of volatile matter content used here was: volatile
and then held constant for 2 min. Finally, the temperature was matter content (ng g1) = peak area of each component  internal
raised by 5 C min1 until it reached 200 C, which was maintained standard concentration (mg mL1)internal standard volume
for 4 min. The temperature of the injector, transfer line, ion source, (lL)  1000/(sample volume  internal standard peak area).
and quadrupole were 250, 260, 230, and 150 C, respectively. The Three measurements for each sample were averaged.
D.-D. Yin et al. / Food Chemistry 187 (2015) 2028 23

2.4. Analysis of avonoids

0.35

0.13

0.42
0.58
0.08

0.06

0.06

0.07
0.08
0.00
0.00

0.00

0.00

0.00

0.00

0.00
33
HPLCDAD analysis was used for the analysis of avonoids, and

0.11
0.19

0.02
0.03

0.04
0.08
0.08
0.05
0.05
0.00
0.00
0.00

0.00
0.00
0.00

0.00
32

was performed with a Dionex P680A HPLC pump, an UltiMate 3000


autosampler, a TCC-100 thermostated column compartment, and a
0.06
0.10
0.02

0.02
0.03

0.10
0.00
0.00
0.00

0.00
0.00

0.00
0.00
0.00

0.00
0.00
31

PDA-100 photodiode array detector, and analyzed with Chameleon


6.60 chromatography workstation software. The HPLC system was
0.15

0.30

0.07

0.04
0.00
0.00
0.00

0.00

0.00
0.00

0.00
0.00
0.00

0.00
0.00
0.00
30

equipped with a 5 lm ODS-80Ts QA C18 column


(4.6 mm  250 mm i.d., Tosoh, Tokyo, Japan). Mobile phases were
0.33
0.08

0.08

0.10
0.00
0.00
0.00
0.00
0.00

0.00
0.00

0.00
0.00

0.00
0.00
0.00
29

10% formic acid aqueous solution containing 0.1% TFA (A) and
0.11

0.20
0.00
0.00
0.00

0.00

0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.1% formic acid in acetonitrile (B). The gradient elution method
28

used was as follows: 8% B at 0 min, 18% B at 15 min, 23% B at


0.19
0.38

0.64
0.08
0.00
0.00
0.00

0.00
0.00
0.00

0.00
0.00
0.00

0.00
0.00
0.00
25 min, 40% B at 45 min, and nally 8% B at 50 min. The ow rate
27

was 0.8 mL min1. Ten microliter analyte aliquots were injected.


0.22

0.47

0.04

0.03
0.00

0.00

0.00
0.00
0.00
0.00

0.00
0.00
0.00

0.00
0.00
0.00
The column temperature was maintained at 35 C for all analyses.
26

Chromatograms were acquired at 350 nm for avonoids, and DAD


0.15

0.22

0.18
0.16
0.19
0.29
0.07
0.09
0.00
0.00
0.00
0.00

0.00
0.00
0.00

0.00

data were recorded from 200 to 800 nm.


25

HPLCESI()-MS/MS analyses of avonoid were carried out with


0.13
0.06

0.07

0.02
0.00
0.00

0.00
0.00
0.00
0.00

0.00
0.00
0.00
0.00
0.00
0.00
24

an Agilent-1100 HPLC system equipped with a UV detector coupled


via an ESI source to an LCMSD Trap VL ion-trap mass spectrome-
0.05
0.09
0.00
0.00
0.00

0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
23

ter (Agilent Technologies, Palo Alto, CA, USA). The HPLC separation
conditions were the same as described above. Both positive-ion
0.16
0.59

0.16
0.19
0.05
0.07

0.03
0.00
0.00
0.00

0.00
0.00
0.00

0.00
0.00

0.00
22

(PI) and negative-ion (NI) ESI mass spectra were acquired. ESI
was performed using a capillary voltage of 4 kV, a nebulization
0.17
0.18
0.16

0.18

0.11
0.22
0.09

0.10
1.06
0.00
0.00
0.00

0.00
0.00

0.00
0.00
21

pressure of 241.3 kPa, and a gas (N2) temperature of 350 C, with


ow rate of 8.0 L min1. The capillary offset and exit voltages were
0.15
0.12

0.19
0.14

0.35
0.15
0.07
0.00
0.00
0.00
0.00

0.00

0.00
0.00

0.00
0.00
20

77.2 V and 127.3 V, respectively, for PI, and 77.2 V and 127.3 V,
0.12

0.06
0.00
0.00
0.00
0.00
0.00
0.00
0.00

0.00

0.00
0.00
0.00
0.00
0.00
0.00

respectively, for NI. The export voltage was 120.4 V. MS and MS/MS
19

spectra were recorded over an m/z range from 100 to 1000.


0.26
0.05
0.09
0.04

0.20
0.05
0.05
0.05
0.08
0.06
0.00

0.00
0.00

0.00
0.00
0.00
18

2.5. Total polyphenol content and evaluation of antioxidant capacity


1.37
0.28

0.15
0.18

0.62
0.19

0.14

0.62
1.04

0.04
0.00
0.00
0.00

0.00

0.00

0.00
17

Total polyphenol content (TPC) in the extracts was evaluated


0.06

0.10

0.06
0.00
0.00
0.00
0.00

0.00
0.00

0.00
0.00
0.00

0.00
0.00
0.00
0.00
16

based on the FolinCiocalteu method (Li et al., 2009). Three assays


0.11

0.27

0.15
0.00
0.00
0.00
0.00

0.00
0.00

0.00

0.00
0.00
0.00
0.00
0.00
0.00

of antioxidant activity were conducted; these included ABTS assay,


15

DPPH assay, and FRAP assay, and were performed according to the
0.05

0.08
0.00
0.00
0.00
0.00

0.00
0.00

0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00

methods reported by Du et al. (2013), Li et al. (2009), and Wang


14

et al. (2014). Each of these four assays used four reference com-
0.14

0.94
0.12

0.11

0.48

0.54
0.10

0.08

0.09
0.20
0.07
0.00

0.00
0.00

0.00
0.00

pounds: gallic acid (GA), ascorbic acid (Vc), 6-hydroxy-2,5,7,8-te-


13

tramethylchroman-2-carboxylic acid (Trolox), and butylated


0.12
0.77

0.11
0.23

0.38
0.24
0.07

0.07

0.07
0.05
0.00
0.00

0.00

0.00

0.00
0.00

hydroxytoluene (BHT) for the generation of standard curves. The


12

TPC and antioxidant activities of the water lily tea infusions were
0.34

0.39
0.11

0.21
0.22

0.14
0.07

0.10

0.09
0.00
0.00

0.00
0.00

0.00
0.00
0.00
11

calculated according to the four standard curves, as the dry weight


of per gram of sample (mg g1). All of the samples were analyzed in
0.13

0.33
0.04

0.07
0.09

0.06

0.09

0.08
0.00
0.00

0.00
0.00

0.00
0.00

0.00
0.00
10

triplicate for each assay.


0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
9

2.6. Statistical analyses


0.13

0.12

0.14
0.05

0.06
0.10
0.00

0.00
0.00
0.00

0.00

0.00
0.00
0.00
0.00
0.00
8

One-way analysis of variance testing (ANOVA) and bivariate


0.12
0.06

0.05

0.06

0.04
0.10
0.00

0.00

0.00
0.00
0.00
0.00
0.00
0.00
0.00

0.00
The avonoid content (ng g1) in water lily tea infusions.

correlation analysis were performed using SPSS 20.0. Post hoc mul-
7

tiple comparisons were executed with an LSD method in the


0.19

0.14
0.10
0.09

0.07

0.09
0.00

0.00

0.00
0.00
0.00
0.00
0.00
0.00

0.00
0.00

ANOVA analysis. The differences were considered to be signicant


6

when P < 0.05. SPSS 20.0 was also used to perform cluster analysis
0.12

0.37

0.13
0.10
0.00

0.00
0.00
0.00
0.00
0.00
0.00

0.00
0.00
0.00
0.00
0.00

and discriminant analysis. The standardized canonical discrimi-


5

nant function coefcients were in Table A.1.


0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
4

0.11
0.15

0.14

0.12
0.43
0.08

0.08

0.10
0.00

0.00

0.00
0.00
0.00
0.00
0.00
0.00

3. Results and discussion


3
Sample No.

0.11
0.08

0.09
0.06

0.10
0.00

0.00

0.00
0.00
0.00

0.00
0.00

0.00
0.00
0.00
0.00

3.1. Identication and quantication of avonoids


2

0.12
0.05

0.08
0.03
0.05

0.03

0.06

0.05
0.00

0.00

0.00

0.00

0.00
0.00

0.00
0.00

Previously, we optimized an HPLCMS method and successfully


1

applied this method for the identication of different avonoids in


Peak No.

water lily tissues (Abulajiang, 2006; Li et al., 2009; Zhu, Zheng


Table 2

f10
f11
f12
f13
f14
f15
f16

et al., 2012). On the basis of these previous studies, the avonoids


f1
f2
f3
f4
f5
f6
f7
f8
f9

in water lily tea infusions were identied by comparing their MS


24
Table 3
Types and concentrations (ng g1) of volatile compounds in water lily tea infusions.

Compounds RT (min) Concentrations (ng/g) of volatile compounds


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19
3-Heptadecene 18.85 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 12.34 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
Lilac alcohol C 18.88 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 3.52 0.00
Benzene,1,4-diethoxy-2-methyl 20.32 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
Z,Z,Z-9,12,15-octadecantrienal 22.25 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
8-Heptadecene 26.60 1.31 3.22 0.00 2.15 8.12 0.00 10.71 41.13 0.00 4.40 3.06 27.91 2.02 44.30 4.89 0.00 0.00 0.00 0.00
Tetradecane 26.60 0.00 0.00 0.00 0.00 6.37 0.00 36.98 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
Bicyclo [3.1.1]hept-2-ene,2,6-dimethyl-6-(4-methyl-3-entenyl)- 27.96 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.26 0.00
Pentadecane 30.89 4.90 6.90 22.59 13.92 28.80 21.71 43.20 31.53 29.65 21.48 12.46 36.98 17.46 33.46 10.34 14.08 7.53 5.19 11.47
alpha-Farnesene 30.98 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
Cyclohexene,3-(1,5-dimethyl-4-hexenyl)-6-methylene- 31.69 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
cis-7-Dodecen-1-yl acetate 33.69 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
Bicyclo[5.3.0]decane 33.70 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.50 1.19 0.00 0.00 0.00 0.00 0.00 0.00 3.26 0.00
Hexadecane 34.76 0.00 0.00 2.46 0.00 0.00 2.77 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 10.92
Bicyclo[2,2,2]octane,2-methyl 37.56 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
Z,Z-10,12-Hexadecadienal 37.57 0.00 0.00 0.00 0.00 0.00 1.74 7.93 0.00 0.00 0.00 0.00 0.00 0.70 247.60 0.00 0.00 0.00 1.09 0.00
cis,cis,cis,-7,10,13-Hexadecatrienal 37.76 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00

D.-D. Yin et al. / Food Chemistry 187 (2015) 2028


Heptadecane 38.95 0.64 0.00 0.00 0.00 5.93 0.00 7.07 0.00 0.00 13.37 2.62 0.00 2.37 8.15 6.71 2.70 0.00 0.00 0.00
6,9-Heptadecadiene 42.09 0.00 0.00 7.31 4.93 4.61 0.00 3.03 0.00 0.00 5.25 0.93 0.00 0.00 3.57 0.00 4.77 5.93 0.00 0.00
Octadecane 42.09 0.00 0.00 0.00 0.00 0.00 4.50 6.11 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
1,6,10-dodecatriene,7,11-diimethyl-3-methylene 43.27 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 12.90 0.00 0.00 0.00 0.00 0.00
Dibutyl phthalate 43.85 0.00 0.00 0.00 0.00 0.00 0.00 9.91 0.00 10.34 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
Nonadecane 44.81 0.36 0.00 0.00 0.00 0.00 2.32 1.56 13.21 6.19 7.62 2.54 3.89 2.12 24.97 12.78 3.73 2.85 0.00 0.00
Caryophyllene 45.16 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
9-Octadecenal,(Z) 47.01 0.00 0.00 0.00 0.00 0.00 0.00 4.65 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
Eicosane 47.01 0.00 0.00 2.90 10.62 0.00 0.00 5.08 0.00 0.00 3.67 2.51 0.00 0.00 1.19 0.00 0.00 0.00 0.00 0.00
1,3,6-Octatriene,1,3,7-trimethyl-(Z,E) 47.60 0.00 0.00 0.00 0.00 0.00 0.00 3.55 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
1,3,6-Heptatriene,2,5,5-trimethyl- 47.60 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.04
Heneicosane 49.57 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 25.00 0.00 0.00 0.00 8.24 0.00 0.00 0.00 0.00 0.00
E-4-(2,6,6-trimethyl-2-cyclohexene-1-yl)-3-butene-2-ketone 49.57 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 6.62 0.00 0.00 0.00 0.00 0.00
Compounds RT (min) Concentrations (ng/g) of volatile compounds
20 21 22 23 24 25 26 27 28 29 30 31 32 33
3-Heptadecene 18.85 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
Lilac alcohol C 18.88 0.00 3.74 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
Benzene,1,4-diethoxy-2-methyl 20.32 0.00 0.00 0.00 40.71 61.70 94.64 0.00 0.00 208.19 0.00 0.00 0.00 0.00 0.00
Z,Z,Z-9,12,15-Octadecantrienal 22.25 0.00 0.00 0.00 0.00 0.00 29.55 13.64 0.00 0.00 21.68 39.44 0.00 0.00 0.00
8-Heptadecene 26.60 5.40 0.00 0.00 0.00 0.00 195.16 6.14 0.00 0.00 112.34 449.31 0.00 43.57 62.07
Tetradecane 26.60 0.00 0.00 2.18 0.00 0.00 0.00 0.00 0.00 0.00 0.00 315.99 0.00 0.00 0.00
Bicyclo [3.1.1]hept-2-ene,2,6-dimethyl-6-(4-methyl-3-entenyl)- 27.96 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 9.18 0.00 0.00 0.00 0.00
Pentadecane 30.89 17.52 6.67 18.44 20.23 47.07 303.58 22.03 5.69 86.82 246.33 0.00 4.33 74.48 167.99
alpha-Farnesene 30.98 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 11.73 7.87 0.00 0.00 13.65
Cyclohexene,3-(1,5-dimethyl-4-hexenyl)-6-methylene- 31.69 0.00 0.00 5.87 2.86 0.00 12.30 0.00 2.83 0.00 10.37 0.00 0.00 0.00 0.00
cis-7-Dodecen-1-yl acetate 33.69 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 300.80
Bicyclo[5.3.0]decane 33.70 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.63 0.00 0.00 947.30 0.00 0.00 0.00
Hexadecane 34.76 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
Bicyclo[2,2,2]octane,2-methyl 37.56 0.00 0.00 0.00 0.00 0.00 111.46 0.00 0.00 0.00 526.89 0.00 0.00 0.00 0.00
Z,Z-10,12-Hexadecadienal 37.57 0.00 1.20 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 151.13 207.02
cis,cis,cis,-7,10,13-Hexadecatrienal 37.76 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 7.27
Heptadecane 38.95 4.73 0.00 0.00 1.82 0.00 11.69 3.49 0.00 0.00 0.00 40.40 1.09 0.00 0.00
6,9-Heptadecadiene 42.09 5.03 0.91 4.34 3.43 0.00 0.00 0.00 0.00 0.00 0.00 0.00 2.81 0.00 0.00
Octadecane 42.09 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
1,6,10-Dodecatriene,7,11-diimethyl-3-methylene 43.27 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 74.58 0.00 0.00 29.81
Dibutyl phthalate 43.85 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
D.-D. Yin et al. / Food Chemistry 187 (2015) 2028 25

and UV spectra with published data. The HPLC chromatograms of a


0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
hardy and a tropical cultivar (Lausanne and Lan He) are shown in
Fig. 1. Table 1 presents information relating to the identication of
33

avonoids based on HPLCDAD analysis (including retention time


and UV absorption maxima) and HPLCESI()-MS/MS analysis
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00
(using data such as molecular ion, aglycone ion, and fragmentation
32

ions observed in MS/MS). We detected various kinds of avonoid


glycosides. In total, 16 avonoids were detected; these could be
7.04
0.00
0.00
0.00
0.00

0.00
0.00
0.00
31

summarized as being based on six aglycone structures (Fig. A1).


The six aglycones included three avonols [quercetin (aglycone
24.16

of compounds f4, f7 and f10), kaempferol (aglycone of compounds


0.00
0.00
0.00
0.00
0.00
0.00
0.00

f9, f15 and f16), and isorhamnetin (aglycone of compounds f2, f3,
30

f8 and f1214)], one avone (aglycone of compounds f1 and f11),


one avanone (aglycone of compounds f6), and one chalcone (agly-
5.91
16.07
0.00
0.00
0.00

0.00
0.00

0.00

cone of compound f5).


29

The avonoid compositions differed among the various culti-


vars. In Madame Wilfron Gonnere, there were 11 avonoids,
165.35
0.00
0.00
0.00
0.00

0.00
0.00
0.00

which was more than in the other cultivars. Arethusa and


28

Somptuosa did not contain any of these compounds. According


to our data, teas prepared from the hardy water lily cultivars con-
1.41

2.73
0.00
0.00
0.00
0.00
0.00
0.00

tained one more type of these avonoids, quercetin 7-O-galac-


27

toside, than did the tropical cultivars. It was notable that


quercetin 3-O-rhamnoside and naringenin 7-O-galactoside were
3.10
0.00
0.00
0.00
0.00
0.00
0.00
0.00

the only avonoid glycosides found in tropical cultivar Hu Die


26

Lan. Chrysoeriol 7-O-glucoside was common in tea infusions of


hardy water lily cultivars but rare in tropical cultivar tea infusions.
6.95
0.00
0.00
0.00
0.00
0.00
0.00
0.00

Kaempferol may exert a profound inhibitory effect on the aging


25

process by inhibiting the generation of reactive oxygen species


via the inhibition of pro-inammatory gene expression (Kim
Concentrations (ng/g) of volatile compounds

38.05
0.00
0.00
0.00
0.00

0.00
0.00
0.00

et al., 2007). The most abundant kaempferol glycoside was kaemp-


24

ferol 3-O-glucosyl-(1 ? 2)-rhamnoside, accounting for more than


two thirds of total kaempferols. The avonoid content in water lily
0.00
0.00
0.00
0.00
0.00
0.00
0.00
0.00

tea infusions of each cultivar is presented in Table 2. Newton had


23

the highest total avonoid content, followed by Madame Wilfron


Gonnere; Sultan had the lowest total avonoid content. Tea vari-
1.86
0.00
0.00
0.00
0.00
0.00
0.00
0.00

ety, weight of tea or teabag, and brewing techniques all affected


22

avonoid intaking (Peterson et al., 2004), so it was essential to


choose cultivars with more avonoids, like Newton and
1.02
0.00
0.00
0.00
0.00
0.00
0.00
0.00
21

Madame Wilfron Gonnere. These two cultivars were potential


materials for making into water lily teas. The total avonoid con-
4.07
0.00
0.00
0.00
0.00
0.00
0.00
0.00

tent in tea infusions of hardy water lily cultivars exceeded the total
20

content in tropical ones. Cultivars with high total avonoids


(>1.00 ng g1) included seven varieties of hardy water lilies, such
RT (min)

as Lausanne, Conqueror, Hollandia, Madame Wilfron


44.81
45.16

49.57
49.57
47.01
47.01
47.60
47.60

Gonnere, Newton, Ellisina, and Virginia; and four tropical culti-


vars (9, Lan He, America, Fo Shou Lian).

3.2. Identication and quantication of volatile compounds


E-4-(2,6,6-trimethyl-2-cyclohexene-1-yl)-3-butene-2-ketone

The types and concentrations of the volatile compounds in the


tea infusions of the 33 water lily cultivars are shown in Table 3.
29 volatile compounds were identied, of which nine compounds
were detected as scent components. The volatile compounds in
the tea infusions were mainly pentadecane, 8-heptadecene, hep-
tadecene, nonadecane and 6,9-heptadecene. Nine scent com-
1,3,6-Octatriene,1,3,7-trimethyl-(Z,E)

pounds were identied as Z,Z-10,12-hexadecadienal, dibutyl


1,3,6-heptatriene,2,5,5-trimethyl-

phthalate, 1,6,10-dodecatriene,7,11-dimethyl-3-methylene (farne-


sene), Z,Z,Z-9,12,15-octadecantrienal, E-4-(2,6,6-3-trimethyl-2-
cyclohexene-1-base)-3-butene-2-ketone, lilacs alcohol C,
caryophyllene, cis-7-dodecen-1-yl acetate, and cis,cis,cis,-7,10,13-
9-octadecenal,(Z)

hexadecatrienal. The volatile compounds included alkanes, olens,


Table 3 (continued)

Caryophyllene

esters, ketones, aldehydes, alcohols, and acids. While the main


Heneicosane
Nonadecane
Compounds

scent components didnt contain alkanes. The scent components


Eicosane

of tea infusions of hardy water lily cultivars were mainly composed


of aldehydes, whereas in the scent components of tea infusions of
tropical water lilies included esters, aldehydes, and alkenes.
26 D.-D. Yin et al. / Food Chemistry 187 (2015) 2028

Furthermore, there were typically more volatile compounds and (2,6,6-trimethyl-2-cyclohexene-1-yl)-3-butene-2-ketone (plea-
scent components in the tea infusions of tropical water lilies than sant) played signicant roles in their divergent fragrances
in infusions of hardy water lilies, a nding consistent with Yuan (Zhang, Chen, Huang, & You, 1999). Among these eight cultivars,
et al. (2014). Therefore, in terms of fragrance, the tea infusions of Zanzibar and Fo Shou Lian gave the relatively rich avors due
tropical water lily cultivars were better than those of hardy water to the high concentrations of scent components, whereas Rene
lily cultivars. Among the 33 cultivars, Fo Shou Lian had the highest Gerard, Ai Ji Bai, and Hu Die Lan held a very delicate fragrance
amount of total scent components at 544.90 ng g1. The results as a consequence of low scent components.
revealed the differences in volatile compounds and scent compo-
nents and concentrations which can guide the application in a- 3.4. Total polyphenol and antioxidant activity
vors and fragrances, scented teas and oral breeding systems in
water lily. The results of both the TPC analysis and the antioxidant activity
assays with the reference standard BHT, Vc, Trolox, and GA are pre-
3.3. Three fragrance patterns sented in Fig. 2. In the case of the assays with GA equivalent, the
TPC ranged from the lowest of 0.77 0.03 mg g1 (Arethusa) to
Concentrations of 29 volatile compounds of water lily tea infu- the highest that was 55 times greater, 43.01 0.85 mg g1
sions were used as variables to perform a hierarchical cluster (Conqueror). The cultivar Conqueror showed signicantly higher
analysis using SPSS 20. Both the furthest neighbor method and TPC than all the other cultivars (P < 0.05).
the cosine clustering method were used, and these generated con- The results of three antioxidant activity assays were similar; all
sistent clustering results. A dendrogram of the clustering results is showed that the cultivar Conqueror and Virginia possessed the
presented in Fig. A2. Based on the origins of the water lily cultivars top two maximal antioxidant activity. This can be attributed to
and the 29 volatile compounds, 33 cultivars were divided into the higher TPC of these two cultivars. There is a close correlation
three clusters. Discriminant analysis was used to divide the 33 between radical scavenging activity and TPC of extracts obtained
water lily cultivars into three groups according to the 29 volatile from various natural sources (Erkan, Ayranci, & Ayranci, 2008).
compounds found in the tea infusions (Fig. A3). The results showed Teas prepared from these two cultivars were compared with vari-
that Steven Strawn, Ray Davies, Lausanne, Arethusa, Perrys ous leafy herbal teas researched by Oh, Jo, Cho, Kim, and Han
Baby Red, Aame, Alba, Somptuosa, Conqueror, Hollandia, (2013). It was found that both cultivars possessed strong antioxi-
Madame Wilfron Gonnere, Marliacea Carnea, Newton, dant activity with the ABTS assay (Conqueror:
Celebration, Ellisina, Virginia, 9, Roxburgh, 18, America, 434.49 mg Vc g1 DW; Virginia: 449.04 mg Vc g1 DW) than other
and Mexicana Zuccarni were grouped together as the rst cat- water extracts of teas, such as green tea (187.36 mg Vc g1 DW),
egory; Princosi, Venusta, Sultan, and Rembrandt were grouped black tea (118.53 mg Vc g1 DW), and peppermint tea
as the second category; and Rene Gerard, Ai Ji Bai, Lan He, Hu (50.08 mg Vc g1 DW). In the case of reference standard BHT
Die Lan, Subra, Royal Purple, Zanzibar, and Fo Shou Lian were equivalent, for the ABTS assay, the maximum and minimum values
grouped as the third category. These results were in accord with were 110.07 0.87 (Virginia) and 2.63 0.86 (Hollandia) mg g1,
the cluster analysis results, with groups 1 and 2 corresponding to respectively; for the FRAP assay, the values ranged from
clusters A and B and consisting mainly of hardy water lilies, while 11.60 0.70 (Somptuosa) to 277.49 5.63 mg g1 (Conqueror);
group 3 corresponded to cluster C and consisted mainly of tropical for the DPPH assay, the BHT of Conqueror was the highest
water lilies. The reason for the differences between clusters A and (103 12.60 mg g1), and that of Somptuosa was the lowest
B requires further investigation. (1.54 0.49 mg g1). All three assays showed that Somptuosa
Cluster A comprised 21 cultivars characterized by a delicate was the least effective antioxidant cultivar. In terms of antioxidant
aroma, containing low scent components and a relatively high activity, the average levels of the tropical water lily cultivars
level of alkanes. Except for Roxburgh and Mexicana Zuccarni, (25.46 mg g1 DW for DPPH; 29.22 mg g1 DW for ABTS+;
each of the other 19 cultivars contained more than 50% alkanes 100.44 mg g1 DW for FRAP) were higher than those for the hardy
of total volatile compounds and alkanes in Aame contributed water lily cultivars (22.94 mg g1 DW for DPPH; 25.33 mg g1 DW
the most with 94.72%. According to our data, lilac alcohol C, which for ABTS+; 77.83 mg g1 DW for FRAP), although there were sev-
was one of the major constituents in the essential oil of Syringa eral cultivars of hardy water lily such as Conqueror and
oblate Lindl (Zhang, Yang, Wang, & Kang, 2011), was only detected Virginia that had very high antioxidant activities. On the whole,
in Celebration and Virginia and was believed to be a characteris- the Conqueror, Virginia, America and Royal Purple cultivars
tic compound described as a fragrance resembling lilac (Matich, displayed relatively high antioxidant activities. These four cultivars
Bunn, Hunt, & Rowan, 2006). Therefore, Celebration and can be used as advantageous cultivars in tea production in the
Virginia were potential materials for producing this scented fra- future.
grance due to their characteristic aroma composition and pleasant
fragrance. Cluster B consisted of four cultivars and possessed simi- 3.5. Correlation analysis
lar smell with cluster A. But the mean values of both alkanes and
olens were higher than cluster A. As shown in Table 3, Z,Z- The correlation coefcients among avonoids, TPC, volatile
10,12-hexadecadienal detected from Sultan was the highest compounds, and antioxidant activity are presented in Table 4.
among 33 cultivars. Madruga, Elmore, Dodson, and Mottram
(2009) reported that decadienal could be applied to improve the
fragrance of meat and produce food avor. So the underlying value Table 4
of Sultan as important fragrance material would be developed in Correlation coefcients of avonoids, volatiles, total polyphenol content and each
antioxidant activity assay.
the future. Cluster C was composed of seven tropical and one hardy
water lily cultivars with a pleasant oral and woody scent. The DPPH ABTS+ FRAP
volatile compounds contributing most to this classication were Flavonoids 0.425 *
0.426* 0.539**
alkanes, olens, aldehyde, and esters. Aromatic compounds such Volatiles 0.097 0.098 0.189
as farnesene (ower with fat), caryophyllene (spic, wood, citrus, TPC 0.933** 0.922** 0.911**

camphor and mild cloves), dibutyl phthalate and cis-7-dodecen- **


Correlation is signicant at the 0.01 level (2-tailed).
1-yl acetate (aroma), cis,cis,cis,-7,10,13-hexadecatrienal, and E-4- *
Correlation is signicant at the 0.05 level (2-tailed).
D.-D. Yin et al. / Food Chemistry 187 (2015) 2028 27

There was a signicantly positive correlation between TPC and Development Program of China (863 Program: Grant No.
antioxidant activity as measured by DPPH (r = 0.933), ABTS+ 2011AA10020702).
(r = 0.922), and FRAP (r = 0.911). This result was in keeping with
earlier reports that stated that plants with higher polyphenolic
Appendix A. Supplementary data
content possess stronger antioxidant activity (Kerio et al., 2013;
Wang et al., 2014). Antioxidant activity was attributed to the phe-
Supplementary data associated with this article can be found, in
nolic contents in plants probably due to their redox properties,
the online version, at http://dx.doi.org/10.1016/j.foodchem.2015.
which allow them to act as reducing agents, hydrogen donors,
04.032.
and singlet oxygen quenchers (Chang et al., 2001). There was a sig-
nicantly positive correlation between avonoid content and
antioxidant activity. This is reasonable, because avonoids are a References
subtype of polyphenols. There was no signicant positive correla-
Abulajiang, K. (2006). Study on the mass spectrometric analytical method of
tion between volatiles and antioxidant activity. This result can be avonoid glycosides. Master Dissertation, Peking Union Medical College,
used to infer that volatile compounds likely contribute little to Beijing, China, pp. 2364.
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This study was nancially supported by the key deployment Anticarcinogenic compounds in the Uzbek medicinal plant Helichrysum
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NO1-16) and the National High Technology Research and compounds in tea. Food Research International, 53, 585599.
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